I don't see any evidence of a crack. I guess I could hit everything. I did find one of the head gaskets on the aft right cylinder with the cylinder ring in the gasket split. I was wondering if that my cause it?

a crack in the head gasket could let water in.

__________________...A bad day water skiing still beats a good day at work...1995 Pro Star 205....

Post a pic of the head gasket. Also the top of the piston in that cylinder.Yes it can cause water in the oil. However if the water was entering through the cylinder, you should have noticed the engine skipping/running rough. Especially at start up after sitting. Also there are areas of the block around the cylinders and water jackets that cannot be seen without pulling the engine and completely disassembling. And sometimes not visible to the naked eye even then. The only way to be certain is complete disassembly and have a machine shop pressure check the block. I suggested the brake clean trick because if you find a crack that way it saves you the trip to the machine shop. The only other option I see is put it back together with new gaskets and run it keeping a close eye on the oil. Not what I would reccomend though.

That head gasket looks like its been blown and not a freeze issue. Do you have a photo of the piston and cylinder head from that side? Is the piston really clean with no carbon on it?

Also, where that ring is broken is right next to a water jacket. You might get away with having the heads surfaced and new gaskets.

I don't have a picture of the piston and cylinder head, but it doesn't really look that much different than the others. I cleaned everything up and looked at all the mating surfaces around the water jackets and I still don't see anything.
I'm at a loss. Where are the most common places these things crack at when they freeze?

I don't see a break between a water and oil passage. Milky oil but no smoke after a pushed freeze plug will almost certainly be a cracked cylinder wall below the piston. That will mean tearing it down and having the cylinder sleeved.

I don't see a break between a water and oil passage. Milky oil but no smoke after a pushed freeze plug will almost certainly be a cracked cylinder wall below the piston. That will mean tearing it down and having the cylinder sleeved.

It did smoke some. Is there any way to verify a cracked cylinder wall below the piston without pulling the engine and tearing it down? Would this show up on a compression test?

It did smoke some. Is there any way to verify a cracked cylinder wall below the piston without pulling the engine and tearing it down? Would this show up on a compression test?

probably not unless there was a crack in the upper half of the cylinder. A leak down test might show trouble. Problem is if you have a normal test, you could still have a crack. Since you are looking at a near total rebuild if you have to tear down and sleeve a cylinder or what ever, you might just replace the head gasket then run it and check for water in the oil every few minutes until the motor is at running temperature. Then do the same thing with the engine under load. No water and you are golden. Water present and you are probably buying a new block!http://www.carcraft.com/techarticles...akdown_tester/

I don't see a break between a water and oil passage. Milky oil but no smoke after a pushed freeze plug will almost certainly be a cracked cylinder wall below the piston. That will mean tearing it down and having the cylinder sleeved.

The clean part of the gasket from the water jacket goes all the way over to the cylinder where the ring is broken and pulled out. If water runs from there it will surely leak past the rings.